Dichloromethane → 4-(Bromomethyl)-2-hydroxybenzonitrile

HRID 379030Notes

Reaction equation

HRID 379030 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>CN(C=O)C>[Br:35][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([OH:1])[CH:9]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 216969742-Hydroxy-4-(hydroxymethyl)benzonitrile

Product 1

HCID 216969934-(Bromomethyl)-2-hydroxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-hydroxy-4-hydroxymethylbenzonitrile (0.20 g, 1.34 mmol) was dissolved in DMF (5 mL) and CH2Cl2(5 mL) and then treated with triphenylphosphine (0.53 g, 2.01 mmol) and carbon tetrabromide (0.67 g, 2.01 mmol) at ambient temperature with stirring. After 2 h, the reaction mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), the organic layer were separated, dried (MgSO4), and filtered to give the title compound after silica gel chromatography (15% EtOAc/hexane to 25% EtOAc/hexane).

Workup

  1. customthe reaction mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
  2. customthe organic layer were separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-315c799a3d5344b990777a7de5cd8fe4
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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